16588-16-2

Usage

Chemical Properties

pale yellow crystalline powder

InChI:InChI=1/C9H8ClNO4/c1-2-15-9(12)6-3-4-7(10)8(5-6)11(13)14/h3-5H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 38818-50-7 4-chloro-3-nitro-benzoyl chloride 
• 96-99-1 4-chloro-3-nitrobenzoate 
• 14719-83-6 methyl 3-nitro-4-chlorobenzoate 
• 75-03-6 ethyl iodide 

Downstream Products

• 55912-20-4 4-chloro-3-nitrobenzyl alcohol 
• 367-80-6 ethyl 4-fluoro-3-nitrobenzoate 
• 71254-73-4 4-morpholin-4-yl-3-nitro-benzoic acid ethyl ester 
• 22057-46-1 ethyl 4-benzylthio-3-nitrobenzoate 
• 629643-57-8 3-nitro-4-(2-oxo-cyclopentyl)-benzoic acid ethyl ester 
• 1027506-75-7 3-nitro-4-(2-oxo-propyl)-benzoic acid ethyl ester 
• 87815-77-8 4-cyclohexylamino-3-nitrobenzoic acid ethyl ester 
• 637041-66-8 ethyl 4-(tert-butylamino)-3-nitrobenzoate 
• 622848-24-2 3-nitro-4-p-toluidino-benzoic acid ethyl ester 
• 312921-97-4 4-benzylamino-3-nitro-benzoic acid ethyl ester 
• 848819-83-0 4-(2,4-dichloro-benzylamino)-3-nitro-benzoic acid ethyl ester 
• 19013-10-6 ethyl 4-hydroxy-3-nitrobenzoate 
• 637041-67-9 ethyl 3-amino-4-(tert-butylamino)benzoate 
• 637041-83-9 ethyl 1-cyclohexyl-1H-benzimidazole-5-carboxylate 

Relevant academic research and scientific papers

Novel [1,2,4]triazolo[3,4-b][1,3,4]thiadiazine derivatives embedded with benzimidazole moiety as potent antioxidants

Fourteen novel [1,2,4]triazolo[3,4-b][1,3,4]thiadiazine derivatives bearing benzimidazole moiety (7a-n) have been synthesized using the one-pot nitro reductive cyclization method. All the synthesized compounds were confirmed by 1H nuclear magne

Hydroxy-benzimidazoles as blue-green emitters: Synthesis, structural and DFT studies

The new benzimidazole ligands (3a-e) were synthesized using ethyl 4-(butylamino)-3-nitrobenzoate and substituted salicylaldehyde in the presence of sodium dithionite reagent which undergoes “one-pot’’ nitro reductive cyclization. Here benzimidazole moiety acts as an electron-acceptor (A) whereas substituted 2-hydroxyphenyl moiety acts as an electron-donor (D) unit. The molecular structures were characterised by FTIR, 1H NMR, 13C NMR, single crystal XRD and MS analysis. Optoelectronic properties were determined by UV–vis, solution and solid photoluminescence, quantum yield and lifetime. The solvent-dependent absorption and emission were studied using both polar protic and polar aprotic solvents. All the derivatives exhibited ESIPT, especially compound ethyl 1-butyl-2-(3,5-dichloro-2-hydroxyphenyl)-1H-benzo[d]imidazole-5-carboxylate (3e) displayed dual emission in both polar protic and polar aprotic solvents. The compound stability and electrochemical property were determined by thermal gravimetric analysis (TGA) and cyclic voltammetry (CV) respectively. The compounds emit intense blue-green fluorescence with high to moderate quantum yield. Also, these derivatives exhibited a high Stokes shift. The computational studies like Density-Functional Theory (DFT) and Molecular Electrostatic Potential (MEP) were conducted to provide important insights into the structure-property relationships. The crystal packing is stabilized through intermolecular hydrogen bonds (C—H…O) and intermolecular interactions (π… π). The findings of results help in developing novel ligands in the field of organic optoelectronics.

Benzo[d]imidazol-5-yl)-5-(substituted)-1,3,4-Oxadiazoles: Synthesis, anticancer, antimicrobial and in silico studies

Background: Cancer is a fatal disease for mankind; continuous research is still going on for the invention of potent anticancer drugs. In this view, 1, 3, 4-Oxadiazoles are privileged molecules which attracted medicinal chemists towards their anticancer p

In vitro, in vivo and in silico-driven identification of novel benzimidazole derivatives as anticancer and anti-inflammatory agents

The synthesis of novel benzimidazole derivatives with varied carbon chain length was achieved via “one-pot” nitro reductive cyclization (6a–o). In each case, compounds were determined by the elemental analyses, FT-IR, mass, 1H and 13

The Suzuki–Miyaura Cross-Coupling as the Key Step in the Synthesis of 2-Aminobiphenyls and 2,2'-Diaminobiphenyls: Application in the Synthesis of Schiff Base Complexes of Zn

2-Nitrophenylboronic acids serve as interesting starting materials for the construction of biphenyl- and terphenyl-based amines if subjected to the Suzuki–Miyaura reaction. Unfortunately, these boronic acids suffer from low reactivity in Suzuki reactions, alongside their low stability in the presence of Pd. Herein, a general method for the construction of 2-nitro-substituted bi- and terphenyls is presented, with special emphasis on the synthesis of 2-amino-2'-nitrobi- and terphenyls. Comparisons are made with other boronic acids that have some of the aforementioned issues. Finally, the application of the obtained 2-amino-2'-nitrobi- and terphenyls as starting materials for the synthesis of bi- and terphenyl based di- and triamines is encountered for, with emphasis on the use of these amines as precursors for Schiff base ligands. In addition, the synthesis of some Zn complexes of these ligands is presented.

Microwave-assisted synthesis of benzimidazole derivatives through nitro reductive cyclization and their biological study

A simple, effective, and eco-friendly synthesis of new benzimidazole-bearing aromatic/heteroaromatic compounds (4 a-o) using sodium dithionite as an effective reductive cyclizing reagent in dimethyl sulfoxide under microwave method is described. The newly

Novel benzimidazole-oxadiazole hybrid molecules as promising antimicrobial agents

In the present study, we describe the design and expeditious synthesis of novel 2-aryl-5-(3-aryl-[1,2,4]-oxadiazol-5-yl)-1-methyl-1H-benzo[d]imidazole hybrid molecules as promising antimicrobial agents. The core moiety 2-aryl-ethyl-1H-benzo[d]imidazole-5-

Novel arylalkylamine compounds exhibits potent selective antiparasitic activity against Leishmania major

Leishmania major (L. major) is a protozoan parasite causal agent of Leishmaniasis. It is estimated that 12 million people are currently infected and around 2 million infections occur each year. Current treatments suffer of high toxicity for the patient, low efficacy toward the parasite, high cost, and are losing effectiveness due to parasite resistance. Discovering novel small molecule with high specificity/selectivity and drug-like properties for anti-leishmanial activity remains a significant challenge. The purpose of this study is to communicate the design and synthesis strategies of novel chemical compounds based of the arylalkylamine scaffold with selective toxicity towards L. major and less toxicity to human cells in vitro. Here, we have developed a structure activity relationship (SAR) study of arylalkylamine AA1 in order to study their anti-parasitic effect in L. major. Overall, 27 arylalkylamine compounds derived from AA1 were synthesized and purified by silica gel column chromatography. The purity of each analog was confirmed by spectroscopic methods (1H, 13C NMR and LC/MS). Among these analogs, the compound AA9 showed the best toxic activity on L. major (LD50 = 3.34 μM), which represents a 9 fold higher lethality as compared with its parental AA1 (Fer-1) compound (LD50 = 28.75 μM). In addition, AA9 showed no significant toxicity at 80 μM on U20S Human Osteoblasts, Raw 264.7 Macrophages or intraperitoneal macrophages. In summary, our combined SAR study and biological evaluation data of AA1-AA27 compounds allow the identification of novel arylalkylamine compound AA9 that exhibits potent cytotoxicity against L. major promastigote with minimum toxic effect on human cells.

BENZOTHIAZIN-3-ONE COMPOUND AND INTERMEDIATE THEREFOR

A medicine which contains as an active ingredient a benzothiazin-3-one-compound represented by the formula (1): (wherein n is 3 or 4; R represents ethyl or hydrogen; and R 1 represents hologeno, alkoxy, haloalkyl, or haloalkoxy) or a pharmaceutically acceptable salt thereof. It is useful as a therapeutic or preventive agent for arthrosis deformans, chondrodegenerative discases such as chronic articular rheumatism, cancers, gingivitis, etc. Also provided are an intermediate for the compound and a process for producing the compound.

INDAZOLES, BENZOTHIAZOLES, BENZOISOTHIAZOLES, BENZISOXAZOLES, AND PREPARATION AND USES THEREOF

The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nACh receptors), activation of nACh receptors, and the treatment of disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds (e.g., indazoles and benzothiazoles), which act as ligands for the α7 nACh receptor subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.